


Milestones and Misunderstandings

by klove0511



Category: Supernatural
Genre: Fluff, M/M, Oblivious!Dean, Sam Winchester Has Self-Worth Issues, Season/Series 14, Tumblr Prompt, inappropriate anniversary gifts, mildly homophobic!Mary, protective!Dean
Language: English
Status: Completed
Published: 2019-01-31
Updated: 2019-01-31
Packaged: 2019-10-19 18:39:56
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,711
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17606804
Author URL: https://archiveofourown.org/users/klove0511/pseuds/klove0511
Summary: There is something different about Sam and Cass. The lingering stares, the intimate touches. The careful whispers and secret smiles. Dean knew it.  He was going to get to the bottom of it, one way or another.





	Milestones and Misunderstandings

**Author's Note:**

> Shoutouts to my awesome betas bananamilkunnie (aka @sweetteamultifandom) and @Revwinchester! Thank you both for checking this over for me. 
> 
> This is for the @Rareshipcreationchallenge Round 24: Naughty or Nice. I had a Naughty prompt: Clone-a-Willy kit. 
> 
> I'm actually surprisingly pleased with how this turned out, so I hope you enjoy it too.

It started innocently. Dean was observant, when he wanted to be, and even he was hard-pressed to ignore how much closer Sam and Cass seemed these days. More than once he’d caught Cass slipping food to Sam in the library or taking lore books from him and ushering him to bed. It stung, a little, that Cass had taken on Dean’s role as big brother in his absence, but Dean couldn’t be too upset. Someone had to watch out for Sam, and Dean had asked Cass to do it, once upon a time. Still, the soft looks between them spoke of something more. Dean considered it his big brother duty to get to the bottom of it and commence teasing as necessary.

Sam was, predictably, in the library with a pile of books in front of him.

“Hey, Sammy,” Dean said, pulling out a chair across from his brother.

Sam blinked at him. “Hey.” He frowned. “What’s going on?”

Dean did his best to sound casual. No need to scare Sammy off. “Nothing. I’ve, uh, just noticed you and Cass have been spending a lot of time together lately.”

“I suppose. He’s been staying close to the bunker for Jack. Well, that and there isn’t any angel business keeping him away for once. We’ve been taking advantage of the time.” Sam frowned. “It’s not too obvious, right? I know everyone from Apocalypse World has accepted Cass, but still. After everything angels have done to them I don’t know how they’d feel if they knew.”

Dean felt rather suddenly like he was all left feet and the conversation had somehow run away from him. “If they knew what? That you and Cass are friends? I think they know, Sam.”

Sam glowered, clearly communicating that he thought Dean was being an idiot on purpose. “No. Obviously I mean,” he waved vaguely, “the _extra_ time we’ve been spending together.”

“What the hell are you—oh.” Suddenly it clicked. “You mean you and Cass are—” Dean also made a vague gesture that he hoped Sam could interpret. Teasing Sam over a crush was one thing, but he was completely unprepared for the possibility that Sam and Cass were already an item, and he couldn’t quite find the words he needed to articulate that.

“Well, yeah. Why do you look surprised? It’s not exactly news.” Sam was frowning hard enough that his worry line had appeared between his eyes.

Dean was struggling to find his footing here. Sam thought he knew. He implied that it wasn’t a new thing. “I don’t—How long?” He hoped that hadn’t sounded too much like an accusation.

“Years.”

“Years?” he choked.

“Yeah. It started after you left that last time. After—after Kevin.”

He remembered that particular black spot in their history too well. Cass had gone back to the bunker with Sam to finish healing the damage from the Trials. He’d thought that was all there was to it. “You’ve been hiding this for five years?

Sam’s face hardened instantly. “I wasn’t hiding anything, Dean. I thought you knew.”

“How the hell was I supposed to know? You never said anything. And you two sure don’t act like a couple. I mean you barely even touch each other.” He was flailing around at this point, but he didn’t care. He’d thought things were better than this between them. It should not have taken him five years to figure out that his little brother was in a serious relationship with his best friend.

“Just because not everyone is into PDA like y—”

“No, Sam. I’m not talking about making out in the halls or whatever, though that would have clued me in real fast. I mean touch—casual touch. Pats on the back or, or holding hands or _something_.” Dean could hear the frustration in his own voice and grimaced internally. This was not how this was supposed to go, but he had a nagging feeling that something was off about this relationship. He needed to get to the bottom of it.

Sam sighed. “It doesn’t matter what it looks like to you, Dean. We touch plenty when no one is watching. Even if we didn’t, I wouldn’t care. I mean—he’s an angel. After everything I’ve— The fact that he even gives me the time of day feels like a miracle.”

There it was. All Dean could hear was that Sam thought he wasn’t good enough, wasn’t worth Castiel’s time. It didn’t matter at all that he knew Sam had struggled with his self-worth over the years, that Dean himself had contributed to those issues as much as anyone. If Cass wasn’t making Sam happy then they needed to have a chat. Dean felt the fury brewing as he stormed out of the library. Time to have a _conversation_ with Cass.

 

Dean ultimately found Cass in the storeroom, doing who knew what with the spell ingredients. “We need to talk,” he growled.

Cass looked up. “Sam said you were upset. What happened?”

“You’re sleeping with my brother!” he accused, finger pointed menacingly as he moved into Cass’s personal space.

Cass tilted his head. “I don’t understand. You know I don’t sl—”

“Sex, Cass. You’re having sex with Sam.”

Castiel straightened and took on a look that was deadly serious. “This bothers you. Why?”

“He’s my brother!”

Cass narrowed his eyes. “And?” When Dean didn’t have words to further clarify the issue with Cass’s eyes blazing at him, he continued. “He is a grown man. I was unaware we needed your permission.”

This conversation was also rapidly spinning out of his control. “It’s not about permission. It’s—Sam has a history with relationships.”

Castiel nodded. “You are referring to Jessica.”

Dean froze at how casually Cass dropped her name. Sam didn’t talk about her, ever. Except he very obviously had with his angel.

Cass continued, “I like to think I am doing rather well. I have come back to life nearly as many times as you.”

Dean frowned. That wasn’t the issue. Or rather, it was only part of the issue. “He thought I already knew. About the two of you. Despite the fact that you act nothing like a couple. And Sam apparently thinks it’s a fucking miracle you want to even talk to him. What the hell kind of relationship do you have?”

Cass’s expression darkened. “One in which I respect Sam’s boundaries. As for his opinion of himself, you think I don’t know? That I am not acutely aware of how little I deserve his affection after everything angels—after everything _I_ have done to him?” He shrugged helplessly. “I cannot convince him.”

That was a surprise. He hadn’t expected Castiel to understand, to want to fix it as much as he did. But if he knew, if he wanted to change things—yeah, Dean could work with this. He remembered what Sam had said about the beginnings of their relationship and did some mental math. “So, tell me, what have you got planned for your anniversary?”

Cass’s confused head tilt told him everything he needed to know.

 

Hours later, Sam and Cass were alone in their room, snuggled on the bed with a Netflix documentary droning in the background. Sam played with the label on his beer bottle while Cass gently carded his fingers through Sam’s hair.

“I just don’t understand why he’s so upset about this,” Sam said. He looked up at Cass. “I really thought he knew.”

“I know. I believed Dean was more concerned about _why_ you did not tell him of our relationship.” Cass let his voice drop even deeper.

Sam sighed heavily. “I didn’t tell him because I was sure he’d figured it out! That’s all!”

Cass’s pace never wavered. No matter how upset Sam became, he maintained his slow, methodical petting, knowing it would help calm Sam. “I believe you. You know how Dean worries. He has not forgotten what I did to your wall.”

Sam stiffened, then pulled himself out of Castiel’s reach. Cass felt his stomach drop in fear. It was a most unpleasant sensation. “Cass, that was years ago. Ancient history.”

Cass spoke softly. “I nearly killed you.” He wouldn’t hide from this. They had never discussed it, not really, and it was past time to do so.

“You saved me.” Sam shook his head. “You—you took on my memories to save my life.”

Cass kept his gaze neutral. “I was simply fixing my greatest mistake. I do not deserve your admiration or gratitude for that. I should never have hurt you, Sam.”

Sam stared at him. The frankness in his gaze was starting to make Castiel uncomfortable, and he thought he understood a little of what Dean had been telling him for years. Finally, he spoke. “You never forgave yourself for that.” His tone was full of wonder and understanding. “Does Dean know?”

Cass nodded. “We discussed many things today. He also enlightened me on the importance of celebrating the beginning of a relationship.”

Sam squinted while he tried to parse that into plain English. “What? The beg—Oh. You mean anniversaries?”

“Apparently they are most important in increments of five.” Cass reached out to pull Sam back into his embrace. Sam went easily and settled against Cass’s chest. “I’m surprised you never mentioned it.”

Sam shrugged. “Dates like that—birthdays, anniversaries—most of them carry bad memories for me. Besides, there’s always been so much going on that it didn’t seem that important, not like other things.”

Cass let his curiosity into his tone. “Other things?”

“You know. All the things we do when we’re actually together. Like this.”

“And intercourse.”

Sam chuckled. “Yeah, that too.” He twisted so he could catch Castiel’s lips.

Cass growled and pulled him tighter. Discussing their anniversary could wait.

 

Dean was drinking whiskey in the kitchen when Mary got home. He didn’t say anything, just raised his glass in acknowledgement.

“Hey. How are you?”

He assumed he looked like crap. Or maybe she just assumed the worst since he was drinking alone. “Fine. Just found out Sam is dating.”

Mary’s eyes widened. “Does he sleep at all? I didn’t think he’d have the time to find someone.”

Dean laughed brightly. It felt good after fighting with Sam all day. “Honestly? No, I don’t think he sleeps. But it’s Cass, so it’s not like he had to find time to go out to bars.”

Mary sank into the seat opposite Dean. “Sam is dating Cass?”

“You didn’t know either. That—actually does make me feel better.” He took a big swallow of his whiskey and winced at the burn. He lifted the bottle to refill his glass and offered it to her.

She waved it off. “I didn’t know Sam was like that.” Her voice was small.

He was a little drunk, so he wasn’t quite following her thread of the conversation. “Yeah, apparently they have been together for five years. Anniversary is tomorrow. I’m helping Cass plan something, but I have no idea what to get them as a gift.”

“It doesn’t bother you?” she asked.

“Sammy and Cass? Nah. I mean, I’m still kind of pissed that they never freaking said anything for five years, but that’s about it. Sam could do way worse. Has. Dude seriously has a thing for monsters though.”

“Do I want to know?” she said.

He shook his head and took a drink. “You really don’t. I mean, I liked Madison too. We didn’t find out she was a werewolf until later. But Ruby. That one was—” He rolled his eyes. “Anyway. Why, does it bother you?” There wasn’t any accusation in his tone, but his senses were starting to wake up. Like he might have to defend Sam.

She gave him a tight smile. “Things are so different these days. I forget sometimes. But he’s my son, and I will always love him. You’re right, he could do much worse than Castiel.”

Dean hesitated, weighing her words, then nodded. “Help me think of a gift for them?” He grinned at her, and she smiled warmly back.

 

Sam entered the dark kitchen and was startled when he realized it was occupied. Castiel was waiting by the table, trench coat conspicuously missing. On the table were some of the plain white candles they kept for spells, arranged in a cluster and lit. The lights were off, leaving the room lit by a soft glow. Something that smelled heavenly was served on the table. Sam knew what this looked like, but he couldn’t quite believe it.

“Cass, what is this?” His voice was softer than he expected.

Castiel smiled broadly. “Happy anniversary, Sam.”

“You cooked?” Sam asked.

“Dean cooked. He planned all of this. I merely agreed to let him do it.” Cass tugged on one of Sam’s hands, pulling him closer. “I thought it was time you had some good memories associated with our anniversary.”

“Thank you.” Sam smiled and brushed his lips against Cass’s.

 

Dinner was amazing, which wasn’t all that surprising since Dean had cooked it. What was more surprising was that Sam realized this was the first proper date they’d had in the whole five years they’d been together. “This was really nice, Cass,” he said.

Cass grinned. “Yes, it was. Dean also informed me that we have the entire bunker to ourselves for the night, and that after dinner I should take you in the library.”

Sam nearly choked on his bite of cheesecake at Castiel’s phrasing, though he was pretty sure the angel hadn’t meant it that way. “The whole bunker? Where is everyone?”

“Hunting, mostly, I believe. Dean and Mary have acquired motel rooms for the night. Jack is with them. And Dean has instructed everyone to check in with them instead of you until tomorrow.”

Just then, Sam’s phone buzzed in his pocket. His eyes widened as he scrambled for his phone. It had been silent all evening and he hadn’t even noticed. This was why he’d never made a big deal out of going on dates or celebrating anniversaries. He could barely handle turning his brain off long enough to get laid. Longer than that and someone was liable to get hurt. He pulled his cell out as he felt Castiel’s hands cover his.

“Everyone is safe, Sam. Dean is taking care of your hunters. You have the night off. Please, can we enjoy it?”

Sam took a deep breath. “Yeah. We can. But I did get a message. Can I?” The earnestness and love he saw in Cass’s eyes were almost painful. He didn’t deserve it.

Cass nodded agreement, and he checked his phone. One message from Dean, confirming everyone had made their check-ins. Everything was fine. He breathed a quiet sigh of relief.

After a moment, Cass took his hand and led him toward the library. Sam was about to say something, when he spotted a package sitting on one of the tables. He automatically reached for the note laying on top of it. He was expecting it to be from Dean, given the lengths to which his brother had apparently gone to give them a nice anniversary. Sure enough, Dean’s neat handwriting fill the sheet.

_Sorry I was such a jerk earlier. It’s not everyday my little brother celebrates a milestone like this, especially with the lives we lead. I know things have been pretty rough the last couple years, and Mom helped me realize you’ve probably spent more time apart than you have together. Knowing our luck, that’s probably going to continue. Hopefully this makes future separations easier. –Dean_

“Wow. This looks weirdly sincere,” Sam said, turning to hand the note to Cass.

Castiel hummed and wrapped Sam in a hug. “I believe Dean mentioned something about taking you in the library. Can it be time for that now?”

Sam chuckled and opened the gift, determined to tease Cass just a little longer. When he finally got a good look at the package, he froze.

Cass piped up from over his shoulder. “I do not understand. What is a Clone-a-Willy kit?”

Sam privately thought he was going to kill Dean. Then again, it had been an amazing night so far. Maybe he would let Dean off the hook, just this once.


End file.
